Hydrochloric Acid → Ethyl 9,10-dihydrophenanthrene-1-carboxylate

HRID 544671ノート

反応式

HRID 544671 の反応式
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[CH:9][C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl.N([O-])=O.[Na+]>C(O)(=O)C.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:11]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]2[CH2:9][CH2:8][C:3]3[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 53977807Ethyl 2-[2-(2-aminophenyl)ethenyl]benzoate

生成物 1

HCID 13281335Ethyl 9,10-dihydrophenanthrene-1-carboxylate収率 43.6%

試薬・触媒・溶媒 3

HCID 24462Copper Sulfate触媒HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒3 回

実験手順

To a stirred solution of ethyl 2-[2-(2-aminophenyl)ethenyl]benzoate (13.5 grams, 0.05 mole) in warm glacial acetic acid (75 ml) was added a solution of concentrated hydrochloric acid (12 ml) in water (10 ml). The mixture was cooled to 0°, and during a 20 minute period a solution of sodium nitrite (3.7 grams, 0.054 mole) in water (30 ml) was added. The resultant mixture was stirred at 0°-5° for three hours. During a 90 minute period the mixture was added to a refluxing solution of copper sulfate (35 grams, 0.14 mole) in water (500 ml). After complete addition, glacial acetic acid (40 ml) was added and the mixture refluxed for one hour. The mixture was cooled to room temperature and extracted with three 200 ml portions of methylene chloride. The extracts were combined, washed with water, and evaporated under reduced pressure to give a brown oil. Distillation of the oil under reduced pressure gave ethyl 9,10-dihydrophenanthrene-1-carboxylate (5.5 grams, bp 145°-165°/0.25 mm) as a yellow oil.

後処理

  1. temperatureThe mixture was cooled to 0°
  2. additionwas added
  3. temperaturethe mixture refluxed for one hour
  4. extractionextracted with three 200 ml portions of methylene chloride
  5. washwashed with water
  6. customevaporated under reduced pressure
  7. customto give a brown oil
  8. distillationDistillation of the oil under reduced pressure

出典と根拠

ORDレコード
ord-9e4f3d0d6aec49d7b10d13d44e2e9e33
出典データセット
uspto-grants-1984_05
特許番号
US04451484

反応ノート

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